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Obstacle Race Calendar near Winchester 2025-2026

Explore the top obstacle runs near Winchester for 2025-2026! We've gathered 96 exciting races in the area. Check out our detailed list below to find your next local race.

November 2025
Nov
23
Sunday

Wobble Before You Gobble 5K

5 km
Nov
23
Sunday

Novemberfest Race for the Nashua Children's Home

Trail Run 4 mi
Nov
27
Thursday

Hingham Turkey Trot

5 km
Nov
27
Thursday

Franklin Park Turkey Trot

5 km
Nov
30
Sunday

Tough 10 Turkey Trot

5 mi 10 mi
December 2025
Dec
6
Saturday

TARC Winter Classic

Trail Run 8 mi 32 mi 40 mi
Dec
6
Saturday

Greater Beverly YMCA Reindeer Run 5K

5 km
Dec
7
Sunday

Happy Holidays Half Merrython

5 km 13 mi
Dec
7
Sunday

Winter Classic

5 km
Dec
7-8
Su - Mo

Jingle Bell Half Marathon

5 km 13 mi
Dec
7
Sunday

Medfield Foundation Angel Run

5 km
Dec
14
Sunday

Somerville Jingle Bell Run

5 km
February 2026
Feb
7-8
Sa - Su

Tarctic Frozen Yeti

Trail Run 15 mi 30 hr
April 2026
Apr
11
Saturday

Merrimack River Trail Race

Trail Run 10 mi
Apr
25
Saturday

TARC Spring Classic

Trail Run 10 km 13 mi 26 mi 50 km
Apr
26
Sunday

James Joyce Ramble 10 Km

10 km
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